Various (meth)acrylate monomers have been employed in hardenable dental compositions.
U.S. Pat. No. 4,648,843 describes polymerizable carbamoyl isocyanurates in filled or unfilled dental materials such as restorative, prosthesis and sealant.
U.S. Pat. No. 5,302,630 describes a dental adhesive composition comprising, as the main components, (a) a polymer powder obtained by radical copolymerization of at least one (meth)acrylate unsaturated monomer containing no carboxyl or anhydride group in its molecule, with a silane compound having a polymerizable unsaturated group, (b) at least one radical polymerizable unsaturated monomer, and (c) a radical polymerization initiator. Column 2 describes an isocyanuric acid skeletal hexa-functional urethane (meth)acrylate as one type of a tri- or higher functional (meth)acrylate monomer containing no carboxyl or anhydride group.
U.S. Pat. No. 6,617,413 describes compounds having isocyanate groups with or without blocking, allophanate groups and free-radically polymerizable C—C double bonds, the C—C double bonds being in activated form by virtue of a carbonyl group attached directly to them or by virtue of an oxygen atom in ether function (activated double bonds), derived from polyisocyanates and alcohols A which in addition to the alcohol group also carry an activated double bond (compounds I). Column 5 depicts iso-cyanurate compounds. Also described is the use of such compound in radiation-curable dental compositions.
EP 2 008 636 relates to a dental composition comprising a) a hardenable compound (A1), b) a filler (B1), c) an initiator (C1) being able to initiate curing of compound (A1), compound (A1) having the structure A-(-S1-U-S2-MA)n, with A being a connector element, S1 being a spacer group comprised of units connected with each other and comprising at least 4 units, S2 being a spacer group comprised of units connected with each other and comprising at least 4 units, U being an urethane, an amide or an urea group connecting spacer groups S1 and S2, MA being an acrylate or methacrylate group and n being 3 to 6. The invention also relates to a process of producing this dental composition and using the dental composition e.g. as a temporary and/or long term crown and bridge material.
US2009/0032989 describes compositions, particularly for forming dental products, having a hardenable self-supporting structure with sufficient malleability to be subsequently customized into a second shape and then hardened, and methods. Paragraph 0026 states that, “In yet another preferred embodiment, a composition of the present invention includes a resin system comprising a crystalline compound of the formula:
wherein each Q independently comprises polyester segments, polyamide segments, polyurethane segments, polyether segments, or combinations thereof; a filler system; and an initiator system; wherein the composition is in the form of a hardenable self-supporting structure having a first shape and sufficient malleability to be formed into a second shape.”
Paragraphs 0135 and 0136 describe polymeric materials derived from the reaction of 1,3,5-tris(2-hydroxyethyl)cyanuric acid and ε-caprolactone. The resulting products were isolated as a solid or as a liquid that solidified.